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It’s not every day that a person loses US$6 billion, so when Michael J. Saylor did exactly that in the 2000s at the height of the internet bubble, he definitely made a name for himself.

Michael J. Saylor lost US$6 billion during the dot-com boom. Photo: @michael_saylor/Instagram
Two decades later though, the 57-year-old CEO and co-founder of business software firm MicroStrategy has ridden the roller coaster all the way back up again. He did so by staking his company’s future on bitcoin – showing even more passion for the world’s biggest cryptocurrency than such tech visionaries as Elon Musk and Jack Dorsey.

So who exactly is Saylor, what is his current net worth and how exactly did he lose billions back in the day? Let’s take a quick dive into the crypto king’s distinctive background.

An early McMoment in Michael Saylor’s life. Photo: @michael_saylor/Instagram
He had an unusual childhood
Born in 1965, in Nebraska, US, Saylor’s childhood was far from average. He grew up in a military family and lived on various US Air Force bases around the world. Graduating as the class valedictorian in high school, the sky was the limit for the young man.

Thanks to a full Air Force scholarship, Saylor obtained dual degrees in aeronautics and astronautics, as well as science, technology and society at the Massachusetts Institute of Technology (MIT). It was also in uni where he met his Theta Delta Chi fraternity brother and future co-founder of MicroStrategy, Sanju K. Bansal.

Michael J. Saylor, chairman and chief executive officer at MicroStrategy at the DC Blockchain Summit in Washington, in May. Photo: Bloomberg
He co-founded MicroStrategy at 24
In 1989, at only 24 years old, Saylor co-founded MicroStrategy, a company that provides business intelligence, mobile software and cloud-based services. Since he couldn’t fulfil his initial dream of becoming a pilot due to a benign heart murmur diagnosis, the tech whizz focused on his passions for technology, business and the use of computer simulations.

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Apart from being a dot-com era entrepreneur, Saylor became an author with his New York Times bestseller, The Mobile Wave: How Mobile Intelligence Will Change Everything. He also founded The Saylor Foundation (now called Saylor Academy) to offer free online courses to those who can’t afford them. He could throw quite the bash too, organising infamous themed yacht parties.

Michael J. Saylor, with one of the trappings of success. Photo: @michael_saylor/Instagram
He became a multibillionaire
In April 2022, Forbes estimated Saylor’s net worth at US$1.6 billion. That sounds pretty impressive for a tech exec, but during the 90s dot-com boom when Saylor rose through the ranks, he reached a whopping net worth of US$7 billion. His multibillionaire status, however, didn’t last long, as it was mostly gone by the turn of the century.

Michael J. Saylor: destined for where? Photo: @michael_saylor/Instagram
He lost US$6 billion in a single day
In early 2000, the US Securities and Exchange Commission (SEC) brought charges against MicroStrategy’s CEO and two other executives for the company’s inaccurate reporting of financial results for the preceding two years. They eventually settled with the SEC, but never admitted any wrongdoing.

Subsequently, Saylor lost his place in the 10-digit club after MicroStrategy revised its financial results and the dot-com bust then crashed the stock.

Will lightning strike Michael J. Saylor twice – the tech world building up his riches, then taking them all away? Photo: Instagram @michael_saylor
He made a major comeback through bitcoin
After 20 years, Saylor put himself on the map again by embracing bitcoin. His belief in the volatile digital currency is so strong that he converted virtually all of MicroStrategy’s cash into the cryptocurrency and personally bought 17,732 bitcoin for US$175 million.

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With bitcoin’s recent plunge, MicroStrategy has lost US$1 billion in investments while Saylor’s net worth reportedly dropped to around US$500 million. Still, the bitcoin bull is not showing any signs of slowing his buying binge soon.`

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“In #bitcoin We Trust,” the CEO of MicroStrategy and crypto king said in a June 13 tweet to his 1.5 million Twitter followers.

Note: This story was originally published on SCMP and has been republished on this website.

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